Sodium methanethiolate → HCID 135786546, compound

HRID 1493031Notes

Reaction equation

HRID 1493031 reaction equation
Cl[CH2:2][C:3]1[N:7]=[C:6]([C:8]2[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([OH:18])=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=2)[O:5][N:4]=1.[CH3:23][S-:24].[Na+]>CO>[CH3:15][C:14]([C:12]1[CH:13]=[C:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][S:24][CH3:23])[N:7]=2)[CH:9]=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[C:11]=1[OH:18])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 135499967HCID 135499967, compound

Product 1

HCID 135786546HCID 135786546, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 2.3 g (0.007 mole) of 4-[3-(chloromethyl)-1,2,4-oxadiazol-5-yl]-2,6-bis(1,1-dimethylethyl)phenol and 0.7 g (0.009 mole) of sodium thiomethoxide in methanol (90 ml) is heated at 75° C. for 1.5 hours. The solution is concentrated to one-third the volume (~30 ml) and diluted with water (50 ml), acidified (pH 4) with 1N hydrochloric acid and extracted with ethyl acetate (2×50 ml). The organic phase is washed with saturated sodium chloride (2×40 ml), dried (anhydrous magnesium sulfate) and evaporated to give a solid. Recrystallization from ethyl acetate and hexane affords 1.3 g (55%) of analytically pure (2,6-bis(1,1-dimethylethyl)-4-[3-[(methylthio)methyl]-1,2,4-oxadiazol-5-yl]phenol, mp 97°-98° C.

Workup

  1. concentrationThe solution is concentrated to one-third the volume (~30 ml)
  2. additiondiluted with water (50 ml)
  3. extractionextracted with ethyl acetate (2×50 ml)
  4. washThe organic phase is washed with saturated sodium chloride (2×40 ml)
  5. dry with materialdried (anhydrous magnesium sulfate)
  6. customevaporated
  7. customto give a solid
  8. customRecrystallization from ethyl acetate and hexane

Sources & evidence

ORD record
ord-3195955394724a14aba2fab756244691
Source dataset
uspto-grants-1994_12
Patent number
US05376670

Reaction notes

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